Synthesis and biological evaluation of curcumin-like diarylpentanoid analogues for anti-inflammatory, antioxidant and anti-tyrosinase activities

Abstract

A series of 46 curcumin related diarylpentanoid analogues were synthesized and evaluated for their anti-inflammatory, antioxidant and anti-tyrosinase activities. Among these compounds 2, 13 and 33 exhibited potent NO inhibitory effect on IFN-gamma/LPS-activated RAW 264.7 cells as compared to L-NAME and curcumin. However, these series of diarylpentanoid analogues were not significantly inhibiting NO scavenging, total radical scavenging and tyrosinase enzyme activities. The results revealed that the biological activity of these diarylpentanoid analogues is most likely due to their action mainly upon inflammatory mediator, inducible nitric oxide synthase (iNOS). The present results showed that compounds 2, 13 and 33 might serve as a useful starting point for the design of improved anti-inflammatory agents.

Preparation of Curcumin-Loaded Liposomes and Evaluation of Their Skin Permeation and Pharmacodynamics

“…The dialysis tubing (molecular weight cutoff of 8,000 to 14,000) was mounted between the donor and the receptor compartments. The cell provided a diffusional area of 0.785 cm 2 , and the receptor compartment was 10 mL. The donor medium consisted of 0.2 mL of vehicle containing different types of liposomes.…”

“…The stirring rate was 400 rpm and the temperature was 37 °C. At different intervals (1,2,4,8,10,12,18,24,36, and 48 h), the receptor samples were removed and replaced with fresh receptor medium. The receptor samples were then analyzed for the drug content by HPLC.…”

“…It has a variety of biological activities and pharmacological actions, such as anti-inflammatory, anti-carcinogenic, and anti-virus properties, as well as promising clinical applications due to its low toxicity [1][2][3]. In recent years, curcumin has been shown to inhibit cell proliferation in a variety of human cancer-cell lines in vitro [4][5][6] and has been used both to prevent and treat various cancers in vivo [7,8].…”

<i>In vitro</i> inhibitory potential of methanolic extract of <i>Celosia argentea</i> var. <i>cristata</i> on tyrosinase, acetylcholinesterase and butyrylcholinesterase enzymes

“…Qualitative phytochemical analysis of crude extract was done for the pre-sence of alkaloids, anthraquinones, coumarins, saponins, flavonoids and tannins as reported elsewhere (Janbaz and Saqib, 2015) Tyrosinase inhibition activity Total volume of reaction mixture 100 μL containing 60 μL phosphate buffer (100 mM), pH 6.8, 10 μL mushroom tyrosinase enzyme (5 units) and 10 μL 0.5 mM test compound mixed in 96-well plate (Lee et al, 2009). Contents were pre incubated for 5 min at 37°C.…”

Molecular docking analysis of curcumin analogues as human neutrophil elastase inhibitors

“…This prompted us to carry out the present study on a selected 17 curcumin analogues among the 47 which were grouped under three major types of a) pentadiene-3-one, b) dibenzyldiene cyclohexanone and c) dibenzyldiene cyclopentanone. Some of these compounds were subsequently reported for various biological activities such as anti-inflammatory, anti-oxidant, anti-tyrosinase (Lee et al, 2009), chemotactic (Jantan et al, 2012) and anti-melanogenesis (Hosoya et al, 2012). The selected compounds are a) 2,5 -bis (2,3-dimethoxy benzylidene) cyclopentanone; b) 2,6 -bis (3,4,5-trimethoxy benzylidene) cyclohexanone; c) 2,6-bis (2,4,6-trimethoxy benzylidene) cyclohexanone; d) 2,6-bis (2,3,4-trimethoxy benzylidene) cyclohexanone; e) 2,6-bis (2,6-dimethoxy benzylidene) cyclohexanone; f) 2,6-bis (2,5-dimethoxy benzylidene) cyclohexanone; g) 2,6-bis (2,4-dimethoxy benzylidene) cyclohexanone; h) 2,6-bis (2,3-dimethoxy benzylidene) cyclohexanone; i) 2,6-bis (benzylidene) cyclohexanone; j) 2,6-bis (4 -hydroxy benzylidene) cyclohexanone; k) 2,6-bis (4-hydroxy-3-methoxy benzylidene) cyclohexanone; l) 1,5-diphenyl-(E, E)-1,4 pentadiene-3-one; l) 1,5-bis (2,4,6-trimethoxy phenyl)-1,4-pentadiene-3-one; m) 1,5-bis (2,6-dimethoxy phenyl)-1,4-pentadiene-3-one; n) 1,5-bis (2,4-dimethoxy phenyl)-1,4-pentadiene-3-one; o) 1,5-bis (2,3-dimethoxy phenyl)-1,4-pentadiene-3-one and p) 1,5 -bis (2-hydroxy phenyl)-1,4-pentadiene-3-one, were evaluated on the docking behaviour of human neutronphil elastase.…”